Methanol → 2-Oxo-1,2,3,4-tetrahydroquinolin-5-yl methanesulfonate

HRID 2058494노트

반응식

HRID 2058494 반응식
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.CO.[OH-].[K+].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>CN(C)C=O>[CH3:17][S:18]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2)(=[O:20])=[O:19]

참가 물질

6

반응물 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chloride2회HCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinone

생성물 1

HCID 128996762-Oxo-1,2,3,4-tetrahydroquinolin-5-yl methanesulfonate수율 38.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

10 g of 5-hydroxy-3,4-dihydrocarbostyril was added to 100 ml of methanol having dissolved therein 3.8 g of potassium hydroxide and the mixture was stirred at room temperature for 30 minutes followed by removing methanol under reduced pressure. Benzene was added to the residue to form crystals and then benzene was removed by evaporation. The residue thus-obtained was suspended in 50 ml of dimethylformamide and 10.6 g of methanesulfonyl chloride was added dropwise to the suspension while ice-cooling with stirring. After adding 3.5 g of methanesulfonyl chloride, the resulting mixture was stirred at room temperature for 4 hours. After the completion of the reaction, the solvent was removed under reduced pressure and the residue was purified through a silica gel column chromatography (silica gel:Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluant:chloroform). Recrystallization of the eluate from water-containing ethanol gave 5.7 g of 5-methanesulfonyloxy-3,4-dihydrocarbostyril as colorless prismatic crystals having a melting point of 227° to 231° C.

후처리

  1. dissolutiondissolved
  2. customby removing methanol under reduced pressure
  3. additionBenzene was added to the residue
  4. customto form crystals
  5. custombenzene was removed by evaporation
  6. customThe residue thus-obtained
  7. temperaturecooling
  8. stirringthe resulting mixture was stirred at room temperature for 4 hours
  9. customAfter the completion of the reaction
  10. customthe solvent was removed under reduced pressure
  11. customthe residue was purified through a silica gel column chromatography (silica gel
  12. customRecrystallization of the eluate from water-
  13. additioncontaining ethanol

출처 및 근거

ORD 기록
ord-bee9db7ca7e84e47badd985fe38af063
출처 데이터셋
uspto-grants-1982_03
특허 번호
US04317820

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